Vacation rentals in Skipwith

4.98 out of 5 average rating, 120 reviews

The living area features a large window with sliding glass doors, allowing natural light to fill the space. A comfortable sofa and coffee table are positioned beside a dining area with chairs. A ceiling fan and subtle grey walls complement the wooden floor, enhancing the atmosphere.

Apartment in Clarksville

Cozy Getaway Efficiency on Buggs Island/Kerr Lake

Fully stocked efficiency on Bluestone Creek, Clarksville, VA. Will sleep 4 (queen bed and sofa sleeper). Best suited for a couple or will accommodate family up to 4. Covered deck overlooking lake. Quiet and secluded, surrounded by 28 acres of woods. Perfect for fishermen and recreation. Parking for boat/ trailer. Dock has electric. A canoe is provided. 15-minute boat ride to Clarksville. Launch is 4 miles from property. Private entrance, 2nd floor. No meals served. Over 10 yrs is an extra guest.

A serene view of Kerr Lake is displayed, with sunlight glimmering on the gentle waves. Bare trees outline the shoreline, while a distant dock is visible against the clear sky, contributing to the tranquil lakeside scenery.

4.9 out of 5 average rating, 151 reviews

TDF Retreat on Kerr Lake

Come enjoy your own space at your own pace, directly on Kerr Lake. Quaint two bdrm/1 bath house on the Lake. 90 minutes from Raleigh or Richmond. This charming home, sleeps five, and is just steps to the dock which you can tie your boat up to. Longwood State Park is the closest boat ramp, and a mere 10 minute boat ride from there. Spend nights watching the sun set and sitting around the firepit making smores. Nonsmoking property. No vehicles on the back lawn. Please review cancellation policy

4.98 out of 5 average rating, 178 reviews

A small rustic cabin features a welcoming porch adorned with string lights. A picnic table and bright blue chair are positioned outside, surrounded by a grassy area and tall trees in the background. The cabin’s red roof contrasts with the white siding.

Farm stay in Hollister

Cozy Cabin & Farm stay @ Owl Tree Acres Homestead

Sunflower cabin is a sweet little rustic cabin with friendly homesteading artist/host located on Owl Tree Acres Farm. Cozy sleeping for 4, a dorm refrigerator, toaster oven, microwave, coffeemaker,. Wifi with desk and Smart HD TV are provided. A “separate” beautiful bath house is located near the Communal fire pit away from the cabin. No bathroom facilities in cabin. Pets allowed with $30 pet fee. No pit bulls, rottweillers or other agressive dog breeds allowed. No pets allowed on beds.

4.93 out of 5 average rating, 180 reviews

A charming sunlit cottage nestled on a green lawn, framed by trees. The structure features large windows, maximizing natural light. A patio with a gazebo is visible in the foreground, providing a relaxing outdoor space. The backdrop includes serene surroundings and hints of Kerr Lake.

Cottage in Clarksville

Lakefront Cottage w/ great view and use of dock

The sunlit cottage is perfect place to enjoy the largest lake in Virginia, exploring nearby state parks, the quaint town of Clarksville, or nearby breweries/wineries. The cottage offers an open view of the lake and use of a dock (150 yds from house) for fishing, swiming, docking watercraft or watching the sunset. A great retreat for a small family of 4 or 2 couples. Please indicate the number of guests; parties over 4 must be pre-approved. Reservation must be by an adult (age 21+).

The screened porch features a colorful area rug with seating options, including four chairs in vibrant hues. Decorative lighting hangs above, adding to the cheerful atmosphere. A small table is placed beside a potted plant, enhancing the inviting and relaxed space.

4.89 out of 5 average rating, 123 reviews

Buggs Island Bungalow

Buggs Island Bungalow One of the oldest residences in Clarksville, the house dates back to the 1800's. We purchased it in 2019 and have lovingly renovated the space and returned it to its former glory. Enjoy all the amenities Clarksville has to offer. Enjoy morning coffee on the screened porch and then stroll to the lake or downtown for antique shopping, and then enjoy a brew at Buggs Island Brewing Company. Please note due to parking constraints we cannot accommodate boat parking.

Superhost

A cozy fire pit area is surrounded by six wooden Adirondack chairs arranged in a circular formation. Lush greenery and sunflower plants frame the space, with clear blue skies and scattered clouds above, creating an inviting spot for outdoor gatherings.

Home in Scottsburg

5 out of 5 average rating, 3 reviews

Relaxing home with big yard right next to park

Very comfortable home with split floor plan with bedrooms on separate sides. Extra large couch for movie nights to relax. Half acre fully enclosed backyard with fire pit to enjoy the night and let your pets run. Plus extra space in backyard screened in with extra TV to watch the game and drink a beer at a homemade bar. Only 1 minute to the state park boat ramp, trails, and quick commute to downtown South Boston. Great for contractors and professionals looking for long-term stay.

Outdoor seating areas are highlighted by colorful chairs surrounding a firepit. A hammock is visible nearby, offering a relaxed space among the trees. The cabin is set back with a spacious deck, nestled within a natural green landscape.

5 out of 5 average rating, 35 reviews

Rooted In Love

Kerr Lake: cozy, super-cute cabin, w/private lake access in neighborhood less than half mile away. Upstairs bedroom, open LR/kitchenette, one bath, in rural VA. Two-burner cooktop & tiny oven (no dishwasher), plus w&d. King bed, plus a daybed w/pop-up trundle in loft; queen foldout sofa downstairs. Rural satellite wi-fi. Boat parking/fish cleaning station. Fenced in dog-run for well-behaved dog. Hammock, firepit & picnic table lakeside! Front porch for sunset and star viewing!

4.98 out of 5 average rating, 134 reviews

A rustic log cabin is nestled among lush greenery, surrounded by trees. A grassy yard extends in front, with a vehicle parked nearby. The structure features multiple windows, showcasing its charming facade and creating a sense of tranquility in the natural setting.

Cabin in Keysville

Peaceful Log Cabin - (Firepit coming Fall-2025)

Privately owned, rustic and quiet log home on 1.5 acres. 10 Minutes from town, 35 minutes to Longwood U and Hampden Sydney College. 20 minutes to Pineview, Waverly and Pavillion @ Mimosa wedding venues. Plenty of room with 2 bedrooms, a fully stocked kitchen, Coffee Bar and separate Tea Bar which are fully stocked. Clean and cozy. The perfect place to unwind, unplug and reset your clock We strive to go above and beyond expectations for your stay. Surprises await!

4.94 out of 5 average rating, 111 reviews

A calm lake scene is depicted, showcasing still waters that reflect the surrounding greenery. Dense trees line the shoreline, creating a serene backdrop. The overcast sky casts a gentle light over the landscape, enhancing the peaceful atmosphere.

Home in Warren County

Peaceful Lakefront Retreat

Enjoy the best Lake Kerr has to offer. Waterfront home with dock and sandy beach. In a quiet cove with deep water perfect for fishing or just sitting by the water watching the sunset- catch catfish right off the dock. Quiet family friendly community located in a peaceful setting. All the conveniences of home provided. Fire pit perfect for s'mores by the water. Lovely water view from the main living areas. Kayaks for use or bring your boat and keep at the private dock.

A private dock is visible extending over the water, featuring two red Adirondack chairs positioned around a small table. Calm lake water can be seen, surrounded by trees and a distant shoreline. A clear sky with scattered clouds completes the serene scene.

4.97 out of 5 average rating, 116 reviews

Perfect Getaway - Waterfront w/ Private Dock

Perfect getaway in this lakefront 2BR/2BA home! Private dock available for your use to enjoy year-round fishing and boating. Explore the quaint town of Clarksville, just 10 minutes away by water or road. Pet friendly. Canoe available for your use! This lakefront house is the perfect retreat for couples, small families, and fishermen! If you like to cook, please help yourself to our herb garden!

4.95 out of 5 average rating, 127 reviews

The historic Bracey Train Depot features a charming white façade with a sloped metal roof. An inviting walkway leads to the front door, framed by a garden area. A large rock sits on a well-maintained lawn, surrounded by trees in the background.

Home in Bracey

Bracey Historic Train Depot

Want to step back in time to the late 1800's? Staying at the historic Bracey Train Depot will give you that experience and more. The Depot is among one of the surviving buildings with the old post office across the street, the general store next door and landmarks. This section of Bracey Drive is at times secluded, just around the 'cut' and a half mile from I-85.